Domino Palladium-Catalyzed Heck-Intermolecular Direct Arylation Reactions

被引：112

作者：

Rene, Olivier ^{[1
]}

Lapointe, David ^{[1
]}

Fagnou, Keith ^{[1
]}

机构：

[1] Univ Ottawa, Ctr Catalysis Res & Innovat, Dept Chem, Ottawa, ON K1N 6N5, Canada

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 20期

基金：

加拿大自然科学与工程研究理事会;

关键词：

ARYL BOND FORMATION; EFFICIENT SYNTHESIS; FUNCTIONALIZATION; CYCLIZATION; ALKYL; ACTIVATION; ARENES; ACIDS;

D O I：

10.1021/ol901799p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A domino palladium-catalyzed Heck-intermolecular direct arylation reaction has been developed, giving access to a variety of dihydrobenzofurans, indolines, and oxindoles, A variety of sulfur-containing heterocycles such as thiazoles, thiophenes, and benzothiophene can be employed as the direct arylation coupling partner in yields up to 99%.

引用

页码：4560 / 4563

页数：4

共 50 条

[1] Assisted ruthenium-catalyzed C-H bond activation: Carboxylic acids as cocatalysts for generally applicable direct arylations in apolar solvents [J].

Ackermann, Lutz ;

Vicente, Ruben ;

Althammer, Andreas .

ORGANIC LETTERS, 2008, 10 (11) :2299-2302

[2] Ruthenium-Catalyzed Regioselective Direct Alkylation of Arenes with Unactivated Alkyl Halides through C-H Bond Cleavage [J].

Ackermann, Lutz ;

Novak, Petr ;

Vicente, Ruben ;

Hofmann, Nora .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (33) :6045-6048

[3] Palladium-Catalyzed Direct Arylations of Heteroarenes with Tosylates and Mesylates [J].

Ackermann, Lutz ;

Althammer, Andreas ;

Fenner, Sabine .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (01) :201-204

[4] Aryl-aryl bond formation by transition-metal-catalyzed direct arylation [J].

Alberico, Dino ;

Scott, Mark E. ;

Lautens, Mark .

CHEMICAL REVIEWS, 2007, 107 (01) :174-238

[5] Tandem Heck-Suzuki-Miyaura reaction: Application to the synthesis of constrained analogues of combretastatin A-4 [J].

Arthuis, Martin ;

Pontikis, Renee ;

Florent, Jean-Claude .

TETRAHEDRON LETTERS, 2007, 48 (36) :6397-6400

[6] Pd-assisted multicomponent synthesis of heterocycles [J].

Balme, G ;

Bossharth, E ;

Monteiro, N .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (21) :4101-4111

[7] The asymmetric Suzuki coupling route to axially chiral biaryls [J].

Baudoin, O .

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2005, 2005 (20) :4223-4229

[8]

BEAUDOIN M, 2007, ORG LETT, V9, P3073

[9] Palladium-catalyzed direct arylation of simple arenes in synthesis of biaryl molecules [J].

Campeau, LC ;

Fagnou, K .

CHEMICAL COMMUNICATIONS, 2006, (12) :1253-1264

[10]

Campeau LC, 2007, ALDRICHIM ACTA, V40, P35

← 1 2 3 4 5 →